


When To Hold, When To Fold

by Sakira_hime



Category: Naruto
Genre: F/M, LOTS of Itachi appreciation, Ocean's Eleven Inspired, also inspired when i was bored out of my mind at a local casino, itcahi appreciation
Language: English
Status: In-Progress
Published: 2017-02-06
Updated: 2017-02-01
Packaged: 2018-09-21 08:42:09
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,613
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9540215
Author URL: https://archiveofourown.org/users/Sakira_hime/pseuds/Sakira_hime
Summary: Originally posted on FF, co-authored by Sahar-Chan and myself up until Chapter 5.Sakura and her team of former mercenaries are tasked with the impossible after their teammate, Sai's brother Shin, is abducted by notorious crime boss Madara Uchiha: Steal from the world's most famous and well-secured casino or risk losing Shin forever. Sakura decides to be the one to go undercover, but it turns out the casino's manager isn't at all what she expected. And his family is even crazier...





	

**Author's Note:**

> Alrighty! This story was first posted on FF but I decided to take it down and repost it here! The amazing Sahar-Chan (FF) co-wrote this with me until Chapter 5 so, enjoy!

She sighed heavily, glancing at her watch periodically as she walked through the spotless halls of the hospital back to her office. 

It had been a gruelling four hour surgery, removing two bullets from a hit and run victim whose heart refused to beat for more than five minutes. But she had been successful. And now, she was beyond tired and more than ready to get back to her apartment. Her life as a doctor was never boring, and she loved the hospital and everything that came with saving lives every day. There was a reason she devoted her life to graduating early and completing her residency as soon as possible, but after a 72 hour shift, three emergency surgeries, and one dead cardiac patient, she was done. Grabbing her handbag and locking her office, she all but sprinted outside and jumped into her car, making it home in record time. Kicking her shoes off just behind the door, she pulled the hairband from her pink hair, letting it fall in tumbles down her back. She sighed deeply and walked over to her answering machine, running tired fingers through her hair and playing her voice messages as she trudged to the kitchen. The beeeeeep echoed through her apartment and rang in her poor, migraine-frazzled ears while she hauled out a pot and threw in some insta-soup, pasta, stuff or whatever. She slumped into a chair at the kitchen table, but her spine snapped to attention the second she heard a very familiar and unexpected voice. Turning to face the direction of her answering machine, she listened with rapt attention. 

“Hey Ugly, this is probably unexpected, but I am in need of your assistance. Everything will be explained, come to my place tomorrow as early as possible. Its urgent.” *Beep. End of messages.* 

She remained seated, staring at the now silent machine hollowly. Sai. She hadn’t seen him in a very long time. If he called, it meant there had to be something, something big and something dangerous. With an exhausted huff, she got up and tugged the pot off the stove plate, eating straight out of the pot. Idly, she wondered whether the rest of the team had been summoned. They’d disbanded years ago, surely most of them had moved on? Well, if it was an emergency and Sai asking, everyone would drop their lives in an instance. Hell, she’d decided to in a heartbeat. Casting a hateful glance at the few dirty dishes in the sink, she turned her nose and went to bed. Tomorrow was going to be big, like PTSD-suffering former drug addict being thrown into a room filled with his/her poison of choice. She needed her rest. Lying in bed, she smiled wryly, silently mourning the loss of her relatively calm life and slipped into a restless slumber, filled with horrors she no longer has the energy to face. ~ “Hey, Ugly.” That damned fake smile was the first thing to greet her when Sai opened the door to his house. She tiredly took in his appearance, noting that his usually alabaster skin was now taut and haggard, and his dark eyes bore purple, bruise-like shadows; a clear sign of stress in its most violent form. Or it was just 5am and her brain was yet to catch up to her. Damn this exhaustion. 

“Hey Sai, how are you? You look…” She glanced at the deep crease between his eyebrows. “Like shit,” she finished, concern lacing her weary voice. He shrugged and moved aside, his gaze dropping to the floor momentarily as she entered. 

Sai’s house was a gorgeous work of art; it was a double story, traditional Japanese styled house. The walls were covered in pieces of Sai’s own work, as well as work by some extremely famous artists. The interior was simple; the floor was covered by a dark blue carpet, and the walls were a washed out grey, making anyone who walked through his house feel calm and safe. She followed him to his living room and, just as she’d expected, almost the entire team was there. Ino sat huddled under a blanket, her blonde hair in some ratty semblance of a bun, just poking out from under the mass of the dark blue fluffiness that was keeping her warm. Next to her sat a very bored-looking Shikamaru, who appeared to be on the cusp of consciousness. On the other two seater, to Sakura’s mild amusement, was Naruto, lying on his stomach, limbs sprawled over the sofa, normally loud mouth ajar and drooling. She actually chuckled softly when she noticed that he practically dwarfed the sofa he lay on. She didn’t have much time to linger on his scrunched up face before Lee swooped in and engulfed her in a hug a mama bear would be proud of. 

“Sakura! You are glowing with the radiance of youth, as usual!” he declared, twirling her around with a blinding smile before setting her down again. 

“Hello to you too, Lee,” she said with a smile. She looked back at her half-fading, half-incapacitated team with a sigh. 

“Up and at em, Naruto!” she called, leaping onto his back and pinching his cheeks wickedly. Her attack thankfully seemed to pull the other two from the edge of sleep and they both watched Sakura torment their sleeping teammate.   
“Mngh, five more minutes, K’kashi,” he grumbled, trying to turn over and consequently remove ‘Kakashi’. But Sakura pinned his arms beneath her knees, and Naruto remained still, face squished into the arm of the sofa. She poked his sides mercilessly, cackling at his pathetic attempts to escape. 

“You’d be glad if it was Kakashi, you lazy shit! Now, why don’t you wake the hell up and greet the prettiest girl you know?” she teased, throwing Ino a mocking wink. Said girl promptly flipped Sakura off and turned her face. Naruto blinked wildly, his bright blue eyes straining to see his attacker from over his shoulder. When he finally saw her, his face broke into a wide smile. 

“Sakura-chan! Jeez, I was wondering when you’d get here. And why do you always have to pinch my cheeks?" he pouted, rubbing his cheek absently and sitting up. Sakura fell into the seat next to him and shrugged. 

“Captain’s orders,” she said, sticking her tongue out at him. “Besides, we’re here for Sai, and you’re out cold on his sofa,” she chided. Sai sat on the arm of Ino’s sofa and addressed Sakura. 

“Where is Kakashi?” 

“Tch, late as usual. I went by his place before I came here, ‘coz I knew he wouldn’t even be up. He said he was right behind me, which means he’ll be here in about an hour and a half. I told him to bring coffee,” she said dismissively. They all knew Kakashi’s habits, Sakura and Naruto most of all. Naruto was Kakashi’s adopted son, and she was his unofficial daughter. Of all her teammates, Kakashi understood her better than all of them put together. So his being late was nothing new. 

“Well, we can start without him, Sai. You look like we need to start right away,” Ino piped up. Sai nodded and took a deep breath. 

“Shin was kidnapped yesterday.” 

There was a beat of silence. 

“And you couldn’t mention it was that serious over the phone?!” Naruto yelled, jumping to his feet and waving his arms about his head. Sakura tugged him back onto the sofa beside her and whacked him over the head for his trouble. 

“Shut up, Naruto. Let Sai finish.”

“As I was saying before dickless over hear interrupted,” he continued, throwing Naruto a pleasantly fake smile. “Shin was kidnapped by a man named Madara. From what I’ve found out, he used to run the Uchiha casinos before he was kicked out for trying to get rid of his partner to take the throne, so to speak.” Sai paused and Sakura chose to speak. 

“I’ve heard of him, he runs a crime syndicate. Word has it he’s legendary, albeit a bit beyond his prime. Still, we can’t underestimate him if he managed to catch Shin off guard.” 

“Exactly,” Sai nodded. “He contacted me through one of his employees yesterday. He’s heard of our team’s, uh, speciality, and wants us to break into the main Uchiha casino, the Mangekyō. We are to rob the primary vault where the casino’s nightly earnings are kept, as well as the family’s personal fortune. He’s given us three months. If we succeed, he’ll release Shin. But if we don’t-“ 

“Wait, so we’re actually gonna do what this psycho wants? Why don’t we bust in and take Shin back ourselves, dammit?!” Naruto roared. The team stilled and turned to watch Naruto’s outrage play across his whisker-marked face. In all honesty, Sakura was certain that most of, if not the entire team had been thinking along those lines. But there were so many variables… 

“Shika, there is a possibility that we could rescue Shin without having to dance around like monkeys for this guy,” she said slowly. Shikamaru appeared to be deep in thought, and the longer he took to reply, the more she regretted agreeing with Naruto. Finally, he lifted his head to look at her seriously. 

“I thought about it while Sai was explaining, and honestly, it is possible.” There were a few murmurs and Naruto’s face split into a wide smile. Sakura’s face remained impassive; there was a catch. 

“But?” she enquired. His lips twitched into a smirk. 

“But,” he began. “I don’t like the danger it would put Shin in. There are too many variables and honestly, we’d need a bigger team for the backup squads. There’s no way I’d send anyone into the lair of a crime syndicate psycho without an armada to support them. That being said, I think we should explore the possibility. There may be something I’ve overlooked.” Sakura doubted that. Shikamaru saw everything, and planned 50 moves ahead of everyone. She nodded and turned to Ino. 

“What do you think, Pig?” Ino narrowed her eyes while chewing on her bottom lip. 

“I have to agree with Shikamaru,” she said. “We have no idea what we’d be walking into, and even if we did, there’s still the possibility that we’d be severely outgunned. But if we were to speak hypothetically, I think Sai could track him easily. Sai?” Sai frowned contemplatively. 

“I’m supposed to relay weekly updates on our progress telephonically. In exchange, I get to speak to Shin for a few minutes.” 

“Perfect,” Ino said, shrugging her blanket-clad shoulders. “He can track the phone, pinpoint the location and we swoop in to rescue Shin. The problem is the lack of an ‘armada’.” 

“I don’t like this,” Sai said suddenly. Everyone turned in their seats to stare at the pale artist. 

“What do you mean, Sai?” Lee asked. 

“I mean that Madara would get wind of our plan somehow and Shin would be dead before we even launched the rescue operation. Our best bet is doing what he asked.” He paused, inhaling deeply before looking at Sakura. 

“I just want my brother back,” he said quietly, his tired eyes pleading. 

“I know, Sai. If you feel that strongly about it, we’ll scrap the rescue mission. Our number one priority is getting Shin home safely, and if the heist is the only way-” 

“We will succeed, Sai,” Shikamaru interrupted, speaking softly. Everyone’s faces turned to him, where he sat practically lounging in his seat, eyes never leaving the ceiling. Sakura nodded in agreement, turning back to Sai. 

“Shika’s right, Sai. There’s no team on earth who could do what we do. We’ll get Shin back, I promise,” she said consolingly. She couldn’t imagine what Sai was feeling now, and his emotionless face didn’t help her conclusion. But she knew what it was like to lose someone precious, so suddenly and violently that the memories forced to the surface threatened to materialize in the form of a panic attack. Her chest caught and her breath hitched minutely, but not enough to be noticed by anyone but Naruto. He gently grabbed her shaking hand and squeezed softly, the warmth of his hand on her icy fingers was enough to chase the shadows away, even for a little while, and she smiled gratefully in return, squeezing his hand in reassurance. 

“Yeah, just have faith, Sai,” Ino said, rubbing Sai’s knee comfortingly. 

“Okay, we know what we’re going to have to do, so let’s get to planning. Shika, I’m assuming that you’ve already got a few brilliant ideas in that giant brain of yours?” Sakura asked teasingly. Said genius grumbled something that sounded kind of like “troublesome woman” before speaking up. 

“The Uchiha’s have always been known for their deep mistrust of anyone who doesn’t bear the same surname, but if this Madara was family, they’ll be on high alert. I have a few ideas, but three months is going to be one hell of a troublesome stretch,” he sighed, scratching his chin in thought. “What I can suggest for now is that you give me two days to work all the kinks out. I’m confident that I’ll be able to lay out a plan that’ll work within three months; I just need to do some research on the casino itself. We still have their blueprints in the archive, right?” he asked, turning his bored gaze from the ceiling to Sakura. She nodded. 

“I’ll have Kakashi give them to you tomorrow, along with the casino’s list of employees. Sai, you can hack their server to get intel on the security detail and lockdown procedures, right?” she asked Sai. He nodded before speaking to Shikamaru. 

“What is your plan?” 

“Hm, so far, one of us will have to pose as a guest, and spend enough time within the casino to pick up staff changes and security procedures. It should take a month, because I’m not sure if they alternate security lockdown procedures every month, or every other month. Most casinos change theirs every other month, but considering the Mangekyō is part of a large chain, I have a feeling they’ll alternate every month. In that case, it may take two months to iron out the details. I know Sai can tag the security cards, that way we’ll know which guards enter the vault and which only deal with the casino floor. As for the person posing as a guest, I think it would be best if it were me. That way I can make alterations to the plan immediately without having to contact everyone else for confirmation. Ino can teach me how to play, and Sakura will be my eyes and ears once Sai hacks the security system. Naruto and Lee, I’ll need you to stay close to the building in case anything goes wrong, or if I need an emergency escape. But I need the prints before I can finalize anything.” 

The team nodded their assent. If anyone could strategize, it was the man whose quick thinking allowed them to snatch over 10 million ryō right from underneath the proudly stingy noses of Iwa National Bank. This was a much bigger and admittedly much more dangerous mission, purely because they’d be sending one of their own inside. But they were professionals, and this was Shin’s life on the line. 

“Yoshi! This will be a challenging mission, but the power of youth is on our side!” Lee’s exclamation was met with five disdainful glances and a soft knock on the front door. Sakura’s eyes widened and she got up, motioning for Sai to sit and walked to the front door. Kakashi was early; he still had another 45 minutes to show. Opening the front door, she burst into a fit of giggles and had to hold onto the door for support. Standing at the door, in all of winter’s glory, was a snow covered Kakashi, clutching frostily onto seven tall coffees wearing the long yellow scarf she’d gotten him as a ski mask. Though she could only see a small part of his face, she could see he was tired, irritable and utterly disgruntled to be more on time than usual. Apparently her little prank worked. 

“M-morning, Kakashi,” she said, trying to muffle her laugh with the back of her hand. He shot her a narrowed glance, shoving past her and into the warmth inside. He shrugged off his scarf and dusted copious amounts of snow from his similarly colored hair and shoulders. Pulling off his leather jacket and tossing it aside, he rounded on her, mask firmly in place. 

“You changed the time on all of my clocks,” he accused coldly. She bit the inside of her cheek to keep from grinning. 

“I don’t know what you’re talking about,” she said innocently, folding her arms in front of her. He raised a scarred brow at her and flicked her nose. 

“You can’t lie to the person who taught you how to,” he admonished, grabbing a coffee and turning to join the rest of her team in the living room. She huffed childishly and stalked after him, slumping back into her seat next to Naruto. 

“Kakashi! What are you doing here so early?” Naruto asked incredulously. Sakura grinned mischievously. 

“He may or may not have had some trouble reading his clocks,” she said evasively, throwing an evil smirk at the masked punctuality-challenged war veteran. He shrugged nonchalantly and engaged Shikamaru in conversation. Sakura smiled at her team. 

They truly were all as fucked up as she was. Naruto lost both his parents in the third war, and Kakashi had taken him in as a way to repay his commander, Minato Namikaze. Sakura had worked with Kakashi in the fourth war, serving as a naval medic. The horrors she had to face were the reasons she suffered from PTSD. But Kakashi understood, and he became a father figure after her own was killed in action. An hour later, when Kakashi was up to speed and everyone had to get ready for work, they left. They decided to meet again at the end of the week to finalize their plans, and once she’d asked Kakashi to get the blueprints for Shikamaru three times, she drove straight to the hospital.

~

The week passed by uneventfully. 

Sakura spent the majority of her time within the sterile walls of the hospital, torturing interns, successfully completing about seven surgeries and even managed to finally find the perfect antibiotic to fight a severe virus going around. All in all, a good week, unless you count the whole ‘Shin kidnap and heist of the century’ fiesta. Thoughts of her recent conversation with Kakashi rolled to the front of her mind as she walked up the steps to Sai’s place in the unforgivingly chilly evening air. He’d phoned her later the same day they’d met to discuss Sai’s dilemma, informing her that her precious blueprints, the ones she’d practically sold her left eyeball for, were nowhere to be found! Digital or otherwise. So they were left with a very big problem, a problem Shikamaru was going to address today. 

She didn’t knock, instead just walked through the door, kicking her shoes off and throwing her black coat over the coat stand. She found her team in the kitchen this time, each member’s hand wrapped snugly around what smelled like a delicious mixture of hot chocolate and cappuccino. She inhaled deeply and sighed in relief. 

“Evening, team,” she greeted, pulling a chair towards the only empty spot at the table left and sitting down. 

“Evening, boss,” Ino chuckled, handing her a mug of the liquid happiness. Sakura nodded in thanks and took a long, wistful gulp, relishing in the warmth that suddenly flowed right through to her fingertips. 

“Okay, Shika, what have you got for me?” she prompted, folding her hands on the table in front of her. Shika leaned forward and mirrored her position. “Well, I don’t have any good news,” he began, studying each person’s face closely. 

“Without the blueprints we’ll be going in blind, and that’s not something any of us are willing to risk. Sai, did you manage to hack the Uchiha mainframe?” 

“Yes, I was successful,” Sai declared, grabbing his laptop and pulling up the hacked server. “As you can see, the details of every employee ever employed or fired, over a period of twenty years are easily accessible. I had some trouble getting past the multiple firewalls but eventually managed to hack into the security system. However, it seems that Mr. Uchiha is a sceptic when it comes to technology.” 

“What makes you say that?” Naruto enquired confusedly. 

“There isn’t a single trace of the casino’s overall layout, blueprints of security procedures. There is evidence that the changes are recorded, and once I managed to decrypt the files, it was obvious that each time there is a change in procedure, the mainframe automatically stores it in a folder that no one can hack, not even me.” 

“Well, shit,” Sakura mumbled. Their plans were going to have change, and drastically too. She glanced at Shikamaru who was pouring over the hacked site with Sai and Kakashi. He’d already planned their next move, in the beginning of the week, in case this happened. But it was a dangerous move, if his carefully blank expression was any indication. What had he planned? 

“Shika, what is your decision?” 

Even as the entirety of the team turned their focused and expected gazes on to him, his own remained fixed on the laptop screen in front of him. He inhaled deeply and exhaled wearily, finally looking up, his dark eyes boring into Sakura’s. 

“You’re not going to like it.”


End file.
